There were the thousands of pilgrims surrounding Jesus, shouting and rejoicing, but observing this unfold were the inhabitants of Jerusalem.…the religious leaders, priests, and governmental officials. As they looked at this massive crowd descending the Mount of Olives, shouting out Messianic prophecies, and following this unassuming man humbly riding on the colt of a donkey, they reacted in a much different way.

It was a pilgrimage to Jerusalem.

Jesus began telling the disciples that He was going to Jerusalem to die months before this trip. The book of Matthew records three separate instances where Jesus told his closest followers of his plan to go to Jerusalem where He would be tried and crucified. The first was when they were in the far north near Caesarea Philippi (Matthew 16:21-23), the second was just after the transfiguration (Matthew 17:22-23), and the third was on the road as they traveled toward Jericho on their way to Jerusalem (Matthew 20:17-19).

The timing of this journey was significant. Jesus was going to Jerusalem for the Passover. Jews from all over the world were making this same trip at the same time. Jesus chose this timing on purpose. Any Jew listening to Matthew being read for the first time would recognize the significance of the timing and would be able to picture in their own minds the events as they unfolded.

Estimates vary widely regarding the year-round population of Jerusalem during the time of Christ. Cousland[i] estimates the population at around 100,000, yet during the Passover Pilgrimage the population could swell to as many as 2-3 million. There was no place in Jerusalem itself to house all the pilgrims. They camped on the hillsides surrounding the city and tens of thousands of campfires covered the hills as people and animals anticipated the Passover observance.

All the main roads to Jerusalem would be packed with hundreds of thousands of people in the week before the Passover. Jesus and the disciples were traveling in this crowd.

The spectacle of the blind men at Jericho.

The last encampment before the final trek to Jerusalem was at Jericho. People would rest, sometimes for a day or two, before they made the final push. The final leg to Jerusalem was an 18 mile hike, with a 3400 foot rise in elevation. It would be like hiking with a full pack with your full family out of the Grand Canyon. The Jericho to Jerusalem hike is 7 miles longer, and two thirds of the elevation rise.

As they camped at Jericho, people recognized Jesus and crowded around Him. They would go in and out of the Jericho to get supplies. It was there that two blind men called out to Jesus to heal them—and He did (Matthew 20:29-33). This would have ignited the crowd. They knew that Jesus was going to Jerusalem, and they hoped that He was the Messiah and something remarkable would happen.

The Jericho Road.

As Jesus and the disciples climbed from Jericho to Jerusalem, there must have been a crowd that surrounded them. The pilgrims traveled in caravans for safety and company. They would sing the Psalms of Ascent to pass the time, build the excitement, and stay encouraged on the grueling final hike.

As they crested the Mount of Olives, Herod’s Temple would burst into full view. This was a sight that many of these pilgrims had longed to see, and many would be seeing it for the first time. Many had to believe that they were not just going to enter the Jerusalem but were going to do so in the company of the promised Messiah.

Jesus chooses to reveal Himself.

As they came to Bethphage, Jesus commanded the disciples to get a donkey and its colt from a nearby village. The crowd watched. When the disciples returned with the donkey and colt and they placed Jesus on it, the crowd burst into a frenzy. They knew this most significant Messianic prophecy of Zechariah 9:9.

Read More